Embodiments of the invention are directed to a system for updating a portable communication device from a media file server. The device automatically orders updating of the media files in a file storage based on detecting the processing of a number of media files and types of possible wireless connections between device and server. In doing this the device removes processed media files, determines an updating volume based on the available storage space in the file storage, requests a transfer of new media files from the server to the device, receives new media files replacing removed media files and stores them in the file storage. The server has a media file archive comprising a number of media files and an archive control unit, which receives the request for transfer, selects new media files that fit into the updating volume and sends them to the device.